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- W2065252662 abstract "The mechanism of the aza-Wittig reaction between phosphazenes and aldehydes has been studied computationally, using DFT methods (B3LYP/6-31G* level), and experimentally. It has been found that the reaction consists of a tandem [2+2] cycloaddition−cycloreversion sequence in which π and σ orbitals as well as lone pairs are involved. Both [2+2] processes take place via thermally allowed supra-supra mechanisms. P-trimethyl-λ5-phosphazenes are predicted to be more reactive than their P-triphenyl analogues. The stereochemical outcome of the whole reaction depends only on the second step, because conformational changes in the intermediate 1,3,2-λ5-oxazaphosphazetidines have a much lower activation energy than the second [2+2] cycloreversion reaction. Preferential or exclusive formation of the corresponding (E)-imines is predicted." @default.
- W2065252662 created "2016-06-24" @default.
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- W2065252662 date "2006-03-02" @default.
- W2065252662 modified "2023-10-16" @default.
- W2065252662 title "Mechanism and Stereoselectivity of the Aza-Wittig Reaction between Phosphazenes and Aldehydes" @default.
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- W2065252662 doi "https://doi.org/10.1021/jo0525884" @default.
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